Nigericin

Names
Preferred IUPAC name

(2R)-2-[(2R,3S,6R)-6-{[(2S,4R,5R,7R,9R,10R)-2-{(2S,2′R,3′S,5R,5′R)-5′-[(2S,3S,5R,6R)-6-Hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-2,3′-dimethyl[2,2′-bioxolan]-5-yl}-9-methoxy-2,4,10-trimethyl-1,6-dioxaspiro[4.5]decan-7-yl]methyl}-3-methyloxan-2-yl]propanoic acid

Other names

Polyetherin A, Azalomycin M, Helixin C, Helix C

Identifiers

CAS Number

* 28380-24-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:7569 Y

ChEMBL |

* ChEMBL405862 Y

ChemSpider |

* 10196461 Y

ECHA InfoCard | 100.212.814

PubChem CID

* 34230

UNII |

* RRU6GY95IS Y

CompTox Dashboard (EPA)

* DTXSID9041079

InChI

* InChI=1S/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1 Y

Key: DANUORFCFTYTSZ-SJSJOXFOSA-N Y

* InChI=1/C40H68O11/c1-21-11-12-28(46-33(21)26(6)36(42)43)17-29-18-30(45-10)27(7)40(48-29)25(5)19-38(9,51-40)32-13-14-37(8,49-32)35-23(3)16-31(47-35)34-22(2)15-24(4)39(44,20-41)50-34/h21-35,41,44H,11-20H2,1-10H3,(H,42,43)/t21-,22-,23-,24+,25+,26+,27+,28+,29+,30+,31+,32+,33+,34-,35+,37-,38-,39-,40+/m0/s1

Key: DANUORFCFTYTSZ-SJSJOXFOBS

SMILES

* OC(=O)[C@H](C)[C@@H]1O[C@H](CC[C@@H]1C)C[C@H]6O[C@]2(O[C@@](C)(C[C@H]2C)[C@H]3CC[C@](C)(O3)[C@@H]4O[C@H](C[C@@H]4C)[C@H]5O[C@@](O)(CO)[C@H](C)C[C@@H]5C)[C@H](C)[C@H](OC)C6

Properties

Chemical formula

| C40H68O11
Molar mass | 724.973 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)

Infobox references

Chemical compound

Nigericin is an antibiotic derived from Streptomyces hygroscopicus. Its isolation from soil from Nigeria was described in the 1950s, by R.L Harned (et. al),[1][2] and in 1968 the structure could be elucidated by X-ray crystallography.[3] The structure and properties of nigericin are similar to the antibiotic monensin. Commercially it is obtained as a byproduct, or contaminant, at the fermentation of geldanamycin. It is also called polyetherin A, azalomycin M, helixin C, antibiotic K178, and antibiotic X-464.

Nigericin acts as an H+, K+, Pb2+ ionophore. Most commonly it is an antiporter of H+ and K+.

In the past nigericin was used as an antibiotic active against gram positive bacteria. It inhibits the Golgi functions in Eukaryotic cells. Its ability to induce K+ efflux also makes it a potent activator of the NLRP3 inflammasome[4][5]

## References

[edit]

1. ^ Harned, R. L.; Hidy, P. H.; Corum, C. J.; Jones, K. L. (December 1951). "Nigericin a new crystalline antibiotic from an unidentified Streptomyces". Antibiotics & Chemotherapy (Northfield, Ill.). 1 (9): 594–596\. ISSN 0570-3123. PMID 24541690.
2. ^ Graven SN, Estrada-O S, Lardy HA (1966). "Alkali metal cation release and respiratory inhibition induced by nigericin in rat liver mitochondria". Proc. Natl. Acad. Sci. U.S.A. 56 (2): 654–8\. Bibcode:1966PNAS...56..654G. doi:10.1073/pnas.56.2.654. PMC 224422. PMID 5229984.
3. ^ Steinrauf LK, Pinkerton M, Chamberlin JW (1968). "The structure of nigericin". Biochem. Biophys. Res. Commun. 33 (1): 29–31\. doi:10.1016/0006-291X(68)90249-0. PMID 5696503.
4. ^ Mariathasan, S; Weiss, DS; Newton, K; McBride, J; O'Rourke, K; Roose-Girma, M; Lee, WP; Weinrauch, Y; Monack, DM; Dixit, VM (9 March 2006). "Cryopyrin activates the inflammasome in response to toxins and ATP". Nature. 440 (7081): 228–32\. Bibcode:2006Natur.440..228M. doi:10.1038/nature04515. PMID 16407890.
5. ^ Muñoz-Planillo, R; Kuffa, P; Martínez-Colón, G; Smith, BL; Rajendiran, TM; Núñez, G (27 June 2013). "K⁺ efflux is the common trigger of NLRP3 inflammasome activation by bacterial toxins and particulate matter". Immunity. 38 (6): 1142–53\. doi:10.1016/j.immuni.2013.05.016. PMC 3730833. PMID 23809161.

* v
* t
* e

Nonribosomally synthesized porters (TC 2B)

* Valinomycin
* Monensin
* Nigericin
* Ionomycin

* v
* t
* e

GABATooltip γ-Aminobutyric acid metabolism and transport modulators

Transporter|

| GATTooltip GABA transporter|

* Inhibitors: 4-Aminovaleric acid
* β-Alanine
* Arecaidine
* CI-966
* DABA
* Deramciclane (EGIS-3886, EGYT-3886)
* EF-1502
* Gabaculine
* Guvacine
* Ibotenic acid
* Muscimol
* Nipecotic acid
* NNC 05-2090
* NO-711
* Riluzole
* SKF-89976A
* SNAP-5114
* TACA
* Tiagabine

|

VIAATTooltip Vesicular inhibitory amino acid transporter|

* Inhibitors: β-Alanine
* Bafilomycin A1
* Chicago sky blue 6B
* Evans blue
* GABA
* Glycine
* N-Butyric acid
* Nigericin
* Nipecotic acid
* Valinomycin
* Vigabatrin

Enzyme|

| GADTooltip Glutamate decarboxylase|

* Inhibitors: 3-Mercaptopropionic acid
* AAOA
* L-Allylglycine
* Semicarbazide

* Activators: 3-Methyl-GABA

|

GABA-TTooltip γ-Aminobutyrate aminotransferase|

* Inhibitors: 3-Hydrazinopropionic acid
* DABA
* γ-Acetylenic-GABA
* AOAA
* EOS
* Gabaculine
* Isoniazid
* L-Cycloserine
* Phenelzine
* PEH
* Rosmarinic acid (lemon balm)
* Sodium valproate
* Valnoctamide
* Valproate pivoxil
* Valproate semisodium (divalproex sodium)
* Valproic acid
* Valpromide
* Vigabatrin

* Activators: 3-Methyl-GABA

Other|

| Antivitamin B6|

* Ginkgotoxin

|

See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Glutamate metabolism/transport modulators

* v
* t
* e

Glutamate metabolism and transport modulators

Transporter|

| EAATsTooltip Excitatory amino acid transporters|

* Amphetamine
* Aspartic acid (aspartate)
* cis-ACBD
* DHKA
* Glutamic acid (glutamate)
* HIP-A
* HIP-B
* Kainic acid
* L-(-)-threo-3-Hydroxyaspartic acid
* L-αAA
* L-CCG-III ((2S,3S,4R)-CCG)
* L-Serine-O-sulphate (SOS)
* L-trans-2,4-PDC
* MPDC
* Maslinic acid
* SYM-2081
* TBOA
* TFB-TBOA
* Theanine
* threo-3-Methylglutamic acid
* UCPH-101
* WAY-213,613

|

vGluTsTooltip Vesicular glutamate transporters|

* 4-Methylene-L-glutamate
* 6-(4'-Phenylstyryl)-QDC
* 6-Biphenyl-4-yl-QDC
* 7-CKA
* Acid red 114
* Amido black 10B (naphthol blue black)
* Bafilomycin A1
* Benzopurpurin 4B
* Bumetamide
* Chicago sky blue 6B
* Aspartic acid (aspartate)
* DIDS
* Direct blue 71
* Erythro-4-methyl-L-glutamic acid
* Evans blue
* Furosemide
* Glutamic acid (glutamate)
* Kynurenic acid
* Nigericin
* NPPB (N144)
* Ponceau SS
* Reactive blue 2
* Rose bengal
* SITS
* trans-ACDP
* Trypan blue
* Valinomycin
* Xanthurenic acid

Enzyme|

| GAHTooltip Glutamine aminohydrolase (glutaminase)|

* BPTES
* CB-839
* DON

|

ASTTooltip Aspartate aminotransferase|

* 2-Amino-3-butenoic acid
* AAOA
* AMB
* β-DL-Methylene-aspartate
* Hydrazinosuccinate

ALTTooltip Alanine aminotransferase|

* β-Chloro-L-alanine
* L-Cycloserine
* Propargylglycine

GDHTooltip Glutamate dehydrogenase|

* AAOA
* Bithionol
* Chloroquine
* EGCG
* GTP
* GW5074
* Hexachlorophene
* Hydroxylamine
* Palmitoyl-CoA
* Pyridoxal phosphate

GSTooltip Glutamine synthetase|

* 2-Aminoadipic acid
* JFD01307SC
* Methionine sulfoximine
* Phosphinothricin (glufosinate)

GADTooltip Glutamate decarboxylase|

* 3-Mercaptopropionic acid
* AAOA
* L-Allylglycine
* Semicarbazide

See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Metabotropic glutamate receptor modulators • GABA metabolism and transport modulators
*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[GABA]: γ-Aminobutyric acid
*[GAT]: GABA transporter
*[VIAAT]: Vesicular inhibitory amino acid transporter
*[GAD]: Glutamate decarboxylase
*[GABA-T]: γ-Aminobutyrate aminotransferase
*[EAATs]: Excitatory amino acid transporters
*[vGluTs]: Vesicular glutamate transporters
*[GAH]: Glutamine aminohydrolase (glutaminase)
*[AST]: Aspartate aminotransferase
*[ALT]: Alanine aminotransferase
*[GDH]: Glutamate dehydrogenase
*[GS]: Glutamine synthetase